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Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C-H Functionalization of o-Vinylphenols

Andrés Seoane, Noelia Casanova, Noelia Quiñones, José L. Mascareñas* and Moisés Gulías*

*CIQUS and Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain , Email: joseluis.mascarenasusc.es, moises.guliasusc.es

A. Seoane, N. Casanova, N. Quiñones, J. L. Mascareñas, M. Gulías, J. Am. Chem. Soc., 2014, 136, 650-652.

DOI: 10.1021/ja410538w (free Supporting Information)


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Abstract

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes in the presence of catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products of a formal (5 + 1) cycloaddition.

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Key Words

benzoxepines


ID: J48-Y2014